CHM243H5S April 2011 Special Deferred Exam

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UNIVERSITY OF TORONTO MISSISSAUGA

APRIL 2011 SPECIAL DEFERRED EXAM
Introductory Organic Chemistry II
CHM243H5S
Patrick T. Gunning
Duration - 3 hours
No Aids allowed
The University of Toronto Mississauga and you, as a student, share a commitment
to academic integrity. You are reminded that you may be charged with an academic
offence for possessing any unauthorized aids during the writing of an exam,
including but not limited to any electronic devices with storage, such as cell phones,
pagers, personal digital assistants (PDAs), iPods, and MP3 players. Unauthorized
calculators and notes are also not permitted. Do not have any of these items in your
possession in the area of your desk. Please turn the electronics off and put all
unauthorized aids with your belongings at the front of the room before the
examination begins. If any of these items are kept with you during the writing of
your exam, you may be charged with an academic offence. A typical penalty may
cause you to fail the course.
Please note, you CANNOT petition to RE-WRITE an examination once you have
begun writing.
Notes to students:

1. Print your name and student at the top of each page.

2. Marks are indicated in parentheses (# marks) after each question.
Total marks equal 100.
3. Be NEAT.
Question Number

1.
2.
3.
4.
5.
6.
7.
Total Marks

MARK

/15
/15
/15
/15
/20
/10
/10
/100
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1. Propose a synthesis for the following compound from phenol. For full marks you should
be able to complete the synthesis in 5 steps or less.

OH

O
NH2

15 Marks

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1. continued:

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2. (i) Fill in the missing reagents/solvents/products. Note that a transformation may require
more than one step. Indicate the work-up as a separate step if required.
10 Marks
O

O
O

O
O

OH

OH

HO

O
O

OH

OH

(ii) Provide a mechanism for step B to C.

5 Marks

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2. continued:

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3. Suggest how you would synthesize compound B from A in 5 steps or less. You will lose
marks for using more than 5 steps.
O
H

15 Marks

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3. continued:

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4. (i) Fill in the missing reagents/solvents/products. Note that a transformation may require
more than one step.
8 Marks
O
1.
1. LDA, THF, -78oC

N
2.

Br

LiAlH4, THF

(1 equiv)

AcOH (acetic acid)

NH2

2. i) NaBH4, EtOH
ii) H3O+ (work up)

B
O

?
D

O
(1 equiv)
NEt3

?
E

(ii) Provide a full mechanism for step C to D including parts 1. and 2.

7 Marks

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4. continued:

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5. (i) Fill in the blanks (including reagents, solvents and reaction conditions)
in the following synthetic scheme. Note that a transformation may require more than one
step.
8 Marks

H
O

OH
O

H3O+

HO

(ii) Provide a full mechanism for the transformation C to D.

12 Marks

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?
D

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5. continued:

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6. Identify the mistakes made in the reaction scheme shown below. Your answer should
include a brief explanation for why the chemical transformation is wrong.
O

O
O

OH

H2N OH
(cat. H3O+)

OH

O
N

NaH (1.1 equivs)

LiOH
H2O

Br
O

1. SOCl2, CH2Cl2

2. NH3
O
NH2
N

NH2

SOCl2

benzene, 80 oC

10 Marks

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6. continued:

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7. Give 4 different sets of reaction conditions that will successfully facilitate the following
transformation shown below.

OH

10 Marks

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Q7. Continued

End of exam

100 marks total

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